Water → HCID 57544762, compound

HRID 2355338Notes

Reaction equation

HRID 2355338 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([CH2:13][C@H:14]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:15]([N:17]([CH3:19])[CH3:18])=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[Na+]>C1COCC1.CCOCC>[CH:7]1([CH2:13][C@H:14]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:15][N:17]([CH3:18])[CH3:19])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 15030061HCID 15030061, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 57544762HCID 57544762, compoundYield 7.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A 1 M solution of LiAlH4 in THF (35 mL, 35.0 mmol) was added to a solution of (S)-tert-butyl 3-cyclohexyl-1-(dimethylamino)-1-oxopropan-2-ylcarbamate (3.85 g, 12.9 mmol) in THF at −78° C. at a rate to maintain the temperature below −60° C. The reaction was permitted to warm to 25° C. and conversion to product was monitored by LC-MS. After 6 h, the reaction was cooled to 0° C., and H2O (3.0 mL) was added dropwise, followed by 1 N aq NaOH (3.0 mL), maintaining the temperature below 10° C. Ether (100 mL) and Celite (10 g) were added to the heterogenous mixture, stirred for 30 minutes and filtered through a pad of Celite. The solvent was removed and the residue was separated on 12 g of SiO2 with an eluent gradient from hexanes to 30% MeOH in EA. Appropriate fractions were combined and the solvent was removed to afford (S)-tert-butyl 1-cyclohexyl-3-(dimethylamino)propan-2-ylcarbamate (0.26 g, 7%) as a white solid. MS ESI+ve m/z 285 (M+Na)+.

Workup

  1. temperatureto maintain the temperature below −60° C
  2. temperaturethe reaction was cooled to 0° C.
  3. temperaturemaintaining the temperature below 10° C
  4. filtrationfiltered through a pad of Celite
  5. customThe solvent was removed
  6. customthe residue was separated on 12 g of SiO2 with an eluent gradient from hexanes to 30% MeOH in EA
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-576ca1f73c8940638013b46baca8db66
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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